BRPI0720439B1 - processos para preparação de acetona cianoidrina - Google Patents
processos para preparação de acetona cianoidrina Download PDFInfo
- Publication number
- BRPI0720439B1 BRPI0720439B1 BRPI0720439A BRPI0720439A BRPI0720439B1 BR PI0720439 B1 BRPI0720439 B1 BR PI0720439B1 BR PI0720439 A BRPI0720439 A BR PI0720439A BR PI0720439 A BRPI0720439 A BR PI0720439A BR PI0720439 B1 BRPI0720439 B1 BR PI0720439B1
- Authority
- BR
- Brazil
- Prior art keywords
- reaction mixture
- loop reactor
- process according
- acetone
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 124
- 238000002360 preparation method Methods 0.000 title claims description 43
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 title description 66
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 144
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 122
- 239000011541 reaction mixture Substances 0.000 claims description 113
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 100
- 238000006243 chemical reaction Methods 0.000 claims description 89
- 239000003054 catalyst Substances 0.000 claims description 72
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 63
- 238000002156 mixing Methods 0.000 claims description 58
- 239000000047 product Substances 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 26
- 239000007795 chemical reaction product Substances 0.000 claims description 22
- 150000001412 amines Chemical class 0.000 claims description 8
- 150000007530 organic bases Chemical class 0.000 claims description 7
- 238000004458 analytical method Methods 0.000 claims description 6
- 238000005070 sampling Methods 0.000 claims description 5
- 150000007529 inorganic bases Chemical class 0.000 claims description 4
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 45
- 239000007789 gas Substances 0.000 description 45
- 238000000746 purification Methods 0.000 description 44
- 238000004821 distillation Methods 0.000 description 39
- 238000005886 esterification reaction Methods 0.000 description 39
- 238000001816 cooling Methods 0.000 description 36
- 150000002148 esters Chemical class 0.000 description 35
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 33
- 230000032050 esterification Effects 0.000 description 31
- 238000009434 installation Methods 0.000 description 29
- 239000003381 stabilizer Substances 0.000 description 25
- 239000000470 constituent Substances 0.000 description 22
- 239000000126 substance Substances 0.000 description 22
- 238000009835 boiling Methods 0.000 description 19
- 239000003153 chemical reaction reagent Substances 0.000 description 16
- 125000005395 methacrylic acid group Chemical group 0.000 description 16
- 238000004064 recycling Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- 238000005406 washing Methods 0.000 description 14
- 239000012071 phase Substances 0.000 description 13
- 238000006116 polymerization reaction Methods 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- 238000007112 amidation reaction Methods 0.000 description 12
- 238000009833 condensation Methods 0.000 description 12
- 230000005494 condensation Effects 0.000 description 12
- 238000003860 storage Methods 0.000 description 12
- 150000001408 amides Chemical class 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- -1 alkyl methacrylates Chemical class 0.000 description 10
- 230000009435 amidation Effects 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 150000002894 organic compounds Chemical class 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 230000003068 static effect Effects 0.000 description 9
- 239000012267 brine Substances 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 7
- 239000002808 molecular sieve Substances 0.000 description 7
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- 238000011144 upstream manufacturing Methods 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000006641 stabilisation Effects 0.000 description 6
- 238000011105 stabilization Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 238000010924 continuous production Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000006189 Andrussov oxidation reaction Methods 0.000 description 4
- 238000013461 design Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005188 flotation Methods 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 238000000265 homogenisation Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 238000004611 spectroscopical analysis Methods 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 206010020649 Hyperkeratosis Diseases 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010411 cooking Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000008394 flocculating agent Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 238000006053 organic reaction Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000013021 overheating Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000012805 post-processing Methods 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 230000008016 vaporization Effects 0.000 description 2
- LVQKOPBJHBWELS-UHFFFAOYSA-N 2-methylpropaneperoxoic acid Chemical class CC(C)C(=O)OO LVQKOPBJHBWELS-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000002033 PVDF binder Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910001069 Ti alloy Inorganic materials 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- OURRXQUGYQRVML-AREMUKBSSA-N [4-[(2s)-3-amino-1-(isoquinolin-6-ylamino)-1-oxopropan-2-yl]phenyl]methyl 2,4-dimethylbenzoate Chemical compound CC1=CC(C)=CC=C1C(=O)OCC1=CC=C([C@@H](CN)C(=O)NC=2C=C3C=CN=CC3=CC=2)C=C1 OURRXQUGYQRVML-AREMUKBSSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000004590 computer program Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000010096 film blowing Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000009751 slip forming Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/16—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same carbon atom of an acyclic carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006058249.7 | 2006-12-08 | ||
| DE102006058249A DE102006058249A1 (de) | 2006-12-08 | 2006-12-08 | Verfahren zur Herstellung von Cyanhydrinen sowie deren Verwendung bei der Herstellung von Methacrylsäurealkylestern |
| PCT/EP2007/059112 WO2008068065A1 (de) | 2006-12-08 | 2007-08-31 | Verfahren zur herstellung von cyanhydrinen sowie deren verwendung bei der herstellung von methacrylsäurealkylestern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BRPI0720439A2 BRPI0720439A2 (pt) | 2014-01-07 |
| BRPI0720439B1 true BRPI0720439B1 (pt) | 2018-11-27 |
Family
ID=38756124
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BRPI0720439A BRPI0720439B1 (pt) | 2006-12-08 | 2007-08-31 | processos para preparação de acetona cianoidrina |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8129559B2 (de) |
| EP (1) | EP2054378B1 (de) |
| JP (1) | JP5290191B2 (de) |
| KR (1) | KR101420462B1 (de) |
| CN (1) | CN101195588A (de) |
| AU (1) | AU2007327789B2 (de) |
| BR (1) | BRPI0720439B1 (de) |
| DE (1) | DE102006058249A1 (de) |
| MX (1) | MX2009005897A (de) |
| MY (1) | MY146961A (de) |
| RU (1) | RU2497805C2 (de) |
| TW (1) | TWI414509B (de) |
| WO (1) | WO2008068065A1 (de) |
| ZA (1) | ZA200903948B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008000787A1 (de) * | 2008-03-20 | 2009-09-24 | Evonik Röhm Gmbh | Verfahren zur Aufreinigung von Methacrylsäure |
| DE102008000785A1 (de) * | 2008-03-20 | 2009-09-24 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Methacrylsäure |
| CN102309985A (zh) * | 2011-10-12 | 2012-01-11 | 大连理工大学 | 用于醛与三甲基氰硅烷的硅氰化反应的高活性催化剂 |
| KR101768854B1 (ko) * | 2013-09-25 | 2017-08-17 | 코닌클리케 필립스 엔.브이. | 탄수화물 함유 식품의 탄수화물 노화를 감소시키기 위한 장치 및 방법 |
| JP6357047B2 (ja) * | 2014-08-05 | 2018-07-11 | 広栄化学工業株式会社 | ニトリル化合物の製造方法 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2000603A (en) * | 1932-02-18 | 1935-05-07 | Eastman Kodak Co | Treatment of cellulosic material prior to esterification |
| US2537814A (en) | 1946-06-14 | 1951-01-09 | American Cyanamid Co | Preparation of acetone cyanohydrin |
| US2731490A (en) | 1953-01-28 | 1956-01-17 | Barsky George | Method of making cyanohydrins |
| US2826601A (en) | 1957-02-05 | 1958-03-11 | Carbogen Corp | System for producing cyanohydrins |
| US3700718A (en) | 1969-11-24 | 1972-10-24 | Sumitomo Chemical Co | Method for continuous production of pure acetone cyanohydrin |
| SU524797A1 (ru) * | 1973-04-11 | 1979-02-05 | Полоцкий Химический Комбинат Им. 50-Летия Белорусской Сср | Способ получени ацетонциангидрита |
| CA1117133A (en) | 1975-05-15 | 1982-01-26 | Michael J. Crosby | Orifice plate mixer and method of use |
| FR2430794A1 (fr) | 1978-07-13 | 1980-02-08 | Ugine Kuhlmann | Perfectionnement aux reacteurs d'hydroformylation |
| EP0022138B1 (de) * | 1979-07-09 | 1983-03-30 | Chemap AG | Schlaufenreaktor zum Begasen von Flüssigkeiten |
| JPH1025273A (ja) * | 1996-07-11 | 1998-01-27 | Asahi Chem Ind Co Ltd | アセトンシアンヒドリンの製造方法 |
| JPH11255710A (ja) * | 1998-03-11 | 1999-09-21 | Mitsubishi Gas Chem Co Inc | メタクリル酸メチルの製造方法 |
| DE19852104A1 (de) | 1998-11-12 | 2000-05-18 | Degussa | Verfahren zur Herstellung von ß-Hydroxyaldehyden |
| DE19918246A1 (de) * | 1999-04-22 | 2000-10-26 | Degussa | Verfahren zur Herstellung von Acetoncyanhydrin |
| US6030534A (en) * | 1999-06-10 | 2000-02-29 | De Lima; Daniel | Three dimensional continuous loop reactor |
| FR2796939B1 (fr) * | 1999-07-29 | 2001-09-14 | Atofina | Procede de fabrication de la cyanhydrine de la methyl ethyl cetone |
| DE10034193A1 (de) | 2000-07-13 | 2002-03-28 | Roehm Gmbh | Verfahren zur Herstellung von Cyanwasserstoff |
| DE10034194A1 (de) | 2000-07-13 | 2003-09-11 | Roehm Gmbh | Verfahren zur Herstellung von Cyanwasserstoff |
| US6790417B2 (en) | 2000-12-21 | 2004-09-14 | Corning Incorporated | Monolith loop reactors |
| DE10118307A1 (de) * | 2001-04-12 | 2002-10-17 | Bayer Ag | Vefahren zur Herstellung von Polycarbonaten |
| EP1325905A1 (de) * | 2001-12-11 | 2003-07-09 | Dsm N.V. | Verfahren zur Herstellung von Bersteinsäuredinitril |
| DE10200171A1 (de) | 2002-01-04 | 2003-07-10 | Roehm Gmbh | Verfahren zur kontinuierlichen Herstellung von Alkyl(meth)acrylaten |
| CN2562866Y (zh) * | 2002-02-01 | 2003-07-30 | 中国石油天然气股份有限公司 | 多级环流反应器 |
| EP1371632A1 (de) | 2002-06-14 | 2003-12-17 | Rohm And Haas Company | Verfahren zur Herstellung von Acetoncyanhydrin |
| AU2003272448A1 (en) | 2002-09-17 | 2004-04-08 | Chevron Phillips Chemical Company Lp | Improved pumping apparatus and process for slurry polymerization in loop reactors |
| DE10309209A1 (de) | 2003-02-28 | 2004-09-09 | Degussa Ag | Verfahren zur Herstellung von Cyanwasserstoff nach dem BMA-Verfahren und Katalysator zu seiner Durchführung |
| DE10323699A1 (de) | 2003-05-22 | 2004-12-09 | Röhm GmbH & Co. KG | Verfahren zur kontinuierlichen Herstellung von Alkylamino(meth)acrylamiden |
| EP1663475B1 (de) * | 2003-09-24 | 2016-11-09 | Basell Polyolefine GmbH | Verfahren mit einem umlaufreaktor mit variiertem durchmesser für die polymerisierung von olefinen |
| DE102004006826A1 (de) | 2004-02-11 | 2005-08-25 | Röhm GmbH & Co. KG | Verfahren zur Herstellung von alpha-Hydroxy-carbonsäuren und deren Ester |
| CN101027276B (zh) | 2004-11-23 | 2011-08-17 | 赢创罗姆有限公司 | 连续制备烷基氨基丙烯酰胺的方法 |
| US7582790B2 (en) * | 2004-11-24 | 2009-09-01 | Rohm And Haas Company | Process for chemical reactions involving cyanohydrins |
| US20060165566A1 (en) * | 2005-01-25 | 2006-07-27 | Fina Technology, Inc. | Loop reactor design |
| DE102005023975A1 (de) | 2005-05-20 | 2006-11-23 | Röhm Gmbh | Verfahren zur Herstellung von Alkyl(meth)acrylaten |
| DE102005023976A1 (de) | 2005-05-20 | 2006-11-23 | Röhm Gmbh | Verfahren zur Umesterung |
-
2006
- 2006-12-08 DE DE102006058249A patent/DE102006058249A1/de not_active Withdrawn
-
2007
- 2007-02-28 CN CNA200710084391XA patent/CN101195588A/zh active Pending
- 2007-08-31 MX MX2009005897A patent/MX2009005897A/es active IP Right Grant
- 2007-08-31 BR BRPI0720439A patent/BRPI0720439B1/pt not_active IP Right Cessation
- 2007-08-31 MY MYPI20091807A patent/MY146961A/en unknown
- 2007-08-31 AU AU2007327789A patent/AU2007327789B2/en not_active Ceased
- 2007-08-31 KR KR1020097011719A patent/KR101420462B1/ko not_active Expired - Fee Related
- 2007-08-31 RU RU2009125686/04A patent/RU2497805C2/ru not_active IP Right Cessation
- 2007-08-31 US US12/515,545 patent/US8129559B2/en not_active Expired - Fee Related
- 2007-08-31 EP EP07803111.9A patent/EP2054378B1/de not_active Not-in-force
- 2007-08-31 WO PCT/EP2007/059112 patent/WO2008068065A1/de not_active Ceased
- 2007-08-31 JP JP2009539673A patent/JP5290191B2/ja not_active Expired - Fee Related
- 2007-12-04 TW TW096146120A patent/TWI414509B/zh not_active IP Right Cessation
-
2009
- 2009-06-05 ZA ZA200903948A patent/ZA200903948B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2497805C2 (ru) | 2013-11-10 |
| MY146961A (en) | 2012-10-15 |
| ZA200903948B (en) | 2010-03-31 |
| KR20090088392A (ko) | 2009-08-19 |
| BRPI0720439A2 (pt) | 2014-01-07 |
| AU2007327789A1 (en) | 2008-06-12 |
| DE102006058249A1 (de) | 2008-06-12 |
| US8129559B2 (en) | 2012-03-06 |
| AU2007327789B2 (en) | 2012-09-20 |
| EP2054378A1 (de) | 2009-05-06 |
| JP5290191B2 (ja) | 2013-09-18 |
| US20100076214A1 (en) | 2010-03-25 |
| MX2009005897A (es) | 2009-06-16 |
| CN101195588A (zh) | 2008-06-11 |
| TWI414509B (zh) | 2013-11-11 |
| WO2008068065A1 (de) | 2008-06-12 |
| JP2010511652A (ja) | 2010-04-15 |
| EP2054378B1 (de) | 2016-02-17 |
| RU2009125686A (ru) | 2011-01-20 |
| TW200831448A (en) | 2008-08-01 |
| KR101420462B1 (ko) | 2014-07-16 |
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